Organic Chemistry
9th Edition
ISBN: 9781305080485
Author: John E. McMurry
Publisher: Cengage Learning
expand_more
expand_more
format_list_bulleted
Question
Chapter 15.SE, Problem 42AP
Interpretation Introduction
Interpretation:
4-Pyrone on treatment with acid gets protonated on the carbonyl group oxygen to yield a stable product. Why the structure is so stable is to be explained using resonance structures and the Huckel’s (4n+2) rule.
Concept introduction:
A compound to become
To explain:
Using resonance structures and the Huckel’s (4n+2) rule why the protonated product obtained when 4-pyrone reacts with acid is so stable.
Expert Solution & Answer
Trending nowThis is a popular solution!
Students have asked these similar questions
OOn a reaction with acid, 4-pyrone is protonated on the
carbonyl-group oxygen to give a stable cationic
product. Using resonance structures and the Huckel
4n+2 rule, explain why the protonated product is so
stable.
4-Pyrone
Write a mechanism that accounts for the formation of ethyl isopropyl ether as one of the products in the following reaction.
CI
OEt
HCI
EtOH
Write the mechanism for step one of this reaction. Show lone pairs and formal charges. Only the acidic hydrogen should
be drawn out with a covalent bond.
Write the mechanism for step two of this reaction (where the product of step one reacts with the solvent, ethanol). Show
lone pairs and formal charges. Only the acidic hydrogen should be drawn out with a covalent bond.
Write the mechanism for the last step of this reaction (formation of ethyl isopropyl ether). Show lone pairs and formal
charges. Only the acidic hydrogen should be drawn out with a covalent bond. CI will act as the base in this reaction.
Provide the correct product(s) for the following reaction
Chapter 15 Solutions
Organic Chemistry
Ch. 15.1 - Prob. 1PCh. 15.1 - Give IUPAC names for the following compounds:Ch. 15.1 - Prob. 3PCh. 15.2 - Pyridine is a flat, hexagonal molecule with bond...Ch. 15.3 - Prob. 5PCh. 15.4 - Draw the five resonance structures of the...Ch. 15.4 - Prob. 7PCh. 15.4 - Prob. 8PCh. 15.5 - Prob. 9PCh. 15.5 - Prob. 10P
Ch. 15.6 - Prob. 11PCh. 15.6 - How many electrons does each of the four nitrogen...Ch. 15.SE - Give IUPAC names for the following substances (red...Ch. 15.SE - All-cis cyclodecapentaene is a stable molecule...Ch. 15.SE - 1, 6-Methanonaphthalene has an interesting 1H NMR...Ch. 15.SE - Prob. 16VCCh. 15.SE - Azulene, an isomer of naphthalene, has a...Ch. 15.SE - Give IUPAC names for the following compounds:Ch. 15.SE - Draw structures corresponding to the following...Ch. 15.SE - Prob. 20APCh. 15.SE - Prob. 21APCh. 15.SE - Draw and name all possible aromatic compounds with...Ch. 15.SE - Propose structures for aromatic hydrocarbons that...Ch. 15.SE - Look at the three resonance structures of...Ch. 15.SE - Prob. 25APCh. 15.SE - Prob. 26APCh. 15.SE - Look at the five resonance structures for...Ch. 15.SE - Prob. 28APCh. 15.SE - 3-Chlorocyclopropene, on treatment with AgBF4,...Ch. 15.SE - Prob. 30APCh. 15.SE - Prob. 31APCh. 15.SE - Prob. 32APCh. 15.SE - Which would you expect to be most stable,...Ch. 15.SE - How might you convert 1, 3, 5, 7-cyclononatetraene...Ch. 15.SE - Calicene, like azulene (Problem 15-17), has an...Ch. 15.SE - Pentalene is a most elusive molecule that has been...Ch. 15.SE - Prob. 37APCh. 15.SE - Prob. 38APCh. 15.SE - Compound A, C8H10, yields three substitution...Ch. 15.SE - Prob. 40APCh. 15.SE - Propose structures for compounds that fit the...Ch. 15.SE - Prob. 42APCh. 15.SE - Prob. 43APCh. 15.SE - N-Phenylsydnone, so-named because it was first...Ch. 15.SE - Prob. 45APCh. 15.SE - Prob. 46APCh. 15.SE - Prob. 47APCh. 15.SE - Propose a structure for a molecule C14H12 that has...Ch. 15.SE - The proton NMR spectrum for a compound with...Ch. 15.SE - The proton NMR spectrum of a compound with formula...Ch. 15.SE - Aromatic substitution reactions occur by addition...Ch. 15.SE - Prob. 52APCh. 15.SE - Consider the aromatic anions below and their...Ch. 15.SE - After the reaction below, the chemical shift of Ha...Ch. 15.SE - Prob. 55APCh. 15.SE - Azo dyes are the major source of artificial color...
Knowledge Booster
Similar questions
- Identify the best reagents to complete the following reaction. HO, CIarrow_forwardWhat is the source of the nucleophilic attack? How does the oxygen get protonated? What causes the elimination reaction?arrow_forwardWhat explains why many aldehydes and ketones can undergo self-condensation reactions in basic conditions? The alpha carbon can lose a proton and act like a nucleophile and the carbonyl carbon is an electrophile. The alpha carbon can gain a proton and act like an electrophile and the carbonyl carbon is a nucleophile. The oxygen of the carbonyl group can attack the carbon of the carbonyl group. Only esters can undergo self-condensation reactions.arrow_forward
- b) The Wolf-Kishner reduction is a reaction used in Organic Chemistry to convert carbonyl functionalities into methylene group. The reaction was used to convert an aldehyde or ketone to an alkane using hydrazine, base and thermal conditions. The mechanism begins with the attack of hydrazine of the aldehyde or ketone. Stage 1: The reaction of aldehyde/ketone with hydrazine to produce hydrazine Stage 2: Reaction with the base and heat to convert hydrozone to alkane Write the mechanism of the reaction.arrow_forwardGive the major product of the following reaction. 1) ВН3/THF 2) H202, NaOHarrow_forwardComplete the Explain what is 1 HBr (no peroxides) HBr peroxides H₂O, H* following reactions of allenes, happeningarrow_forward
- Provide a structure for the major products of the reactions and include the steps for each reaction.arrow_forwardExplain why pentane-2,4-dione forms two alkylation products (A and B) when the number ofequivalents of base is increased from one to two.arrow_forwardDraw the structure of the major organic product(s) of the reaction. -N H3O+arrow_forward
- Draw a structure for the major organic product you would expect from reaction of 3-methyl-3-pentanol with NaH.arrow_forward1) Nucleophilic substitution reaction of alkyl halide is a process when nucleophile replace the leaving group of alkyl halide. Propose the mechanism and product(s) for the following substitution reaction.arrow_forwardChoose the best reagents for the following reaction.arrow_forward
arrow_back_ios
SEE MORE QUESTIONS
arrow_forward_ios
Recommended textbooks for you